CN112094220A - Green synthesis method of 3-sulfone methyl-1H-indole compound - Google Patents
Green synthesis method of 3-sulfone methyl-1H-indole compound Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
Abstract
The invention discloses a green synthesis method of a 3-sulfone methyl-1H-indole compound. The structure of the 3-sulfone methyl-1H-indole compound is shown as a formula I; the preparation process comprises the following steps: with R1Substituted 3-indoleacetic acid compounds and R2The substituted sodium sulfinate compound is used as a raw material, a copper catalyst is adopted, N-dimethylformamide or dimethyl sulfoxide is used as a solvent, nitrogen is used for protection, and the reaction is heated to generate the 3-sulfone methyl-1H-indole compound shown in the formula I. The method takes N, N-dimethylformamide or dimethyl sulfoxide as a solvent, adopts a copper catalyst, and avoids using an expensive or complex catalyst; the reaction condition is mild, the reaction process is simple, and the green chemical concept is met; the post-treatment of the reaction is simple, and the high-purity 3-sulfone methyl-1H-indole compound can be obtained only by simple extraction, concentration and column chromatography.
Description
Technical Field
The invention relates to the technical field of organic synthesis, and particularly relates to a green synthesis method of a 3-sulfone methyl-1H-indole compound.
Background
Indole and derivatives thereof are important nitrogen heterocyclic compounds, have wide biological activities such as anti-inflammation, analgesia and the like, are effective intermediates of a plurality of natural products and pharmaceutically active molecules, and are a great hot spot of current pharmaceutical research. In recent years, with the development of green chemistry, methods for synthesizing aryl indole, alkenyl indole, alkyl indole, thioether indole compounds, and the like have been remarkably developed. (L.S.; P.A.; P.M.chem.Rev.2014,114, 7108; D.R.chem.Soc.Rev.2015,44,742-778.) but less methods of synthesizing sulfone methyl substituted indoles have been reported. Therefore, the synthesis of 3-sulfonemethyl-1H-indole compounds is challenging and of research value.
3-Indolylacetic acid is present in many biologically active compounds, such as sulindac, indomethacin, and the like. On the other hand, sulfone groups are not only one of the most common functional groups in organic synthesis, but also important components of various drug molecules. Methods for synthesizing 3-sulfonemethyl 1H-indole compounds have been reported: 1. oxidation of 3-thiomethyl or sulfoxymethyl 1H-indole compounds; 2. lu et al have recently reported iron-catalyzed sulfonation methylation of indoles in water-polyethylene glycol. (Lu.S.; Zhu.Y. -S.; Yan.K. -X.; cui.T. -W.; Zhu.X.; Hao.X. -Q.; Song.M. -P.Synlett.2019,30,1924-1928.) however these syntheses still suffer from disadvantages: expensive raw materials, a large amount of organic solvents, complicated synthetic steps, etc. are required.
Therefore, the development of a green synthesis method of the 3-sulfomethyl-1H-indole compound has important significance for the development of synthesis methodology and pharmaceutical chemistry.
Disclosure of Invention
The invention aims to provide a green synthesis method of a 3-sulfomethyl-1H-indole compound, aiming at the defects that in the prior art, the preparation of the 3-sulfomethyl-1H-indole compound needs to be carried out in multiple steps, each step of reaction needs to consume a large amount of organic solvent, metal catalyst and the like, and the 3-sulfomethyl-1H-indole compound has complex reaction conditions, more side reactions, difficult product separation and the like. The method takes a substituted 3-indoleacetic acid compound and a substituted sodium sulfinate compound as raw materials, adopts a copper catalyst, takes N, N-dimethylformamide or dimethyl sulfoxide as a solvent, and carries out reaction under the protection of nitrogen, thus obtaining the 3-sulfone methyl-1H-indole compound; the preparation method has mild reaction conditions, and the used catalyst is copper acetate, so that the use of expensive and complex catalysts is avoided, and the preparation method conforms to the green chemical concept.
The above object of the present invention is achieved by the following scheme:
a green synthesis method of a 3-sulfone methyl-1H-indole compound, wherein the structure of the 3-sulfone methyl-1H-indole compound is shown as a formula I:
wherein R is1Is hydrogen, halogen, alkyl or alkoxy; r2Is alkyl, phenyl or substituted phenyl;
the preparation process comprises the following steps: with R1Substituted 3-indoleacetic acid compounds and R2The substituted sodium sulfinate compound is used as a raw material, a copper catalyst is adopted, N-dimethylformamide or dimethyl sulfoxide is used as a solvent, nitrogen is used for protection, and the reaction is heated to generate the 3-sulfone methyl-1H-indole compound shown in the formula I.
In the preparation method of the invention, R1The substituted 3-indoleacetic acid compound firstly generates a bivalent copper complex under the catalysis of copper acetate; then, carrying out oxidative decarboxylation reaction on the divalent copper complex and substituted sodium sulfenate to obtain a 3-sulfone methyl-1H-indole compound; according to the preparation method, specific raw materials are adopted, a copper catalyst and N, N-dimethylformamide or dimethyl sulfoxide are adopted as solvents, nitrogen is protected, the substituted 3-indoleacetic acid compound and the substituted sodium sulfinate compound can be subjected to oxidative decarboxylation reaction, the 3-sulfomethyl-1H-indole compound can be prepared through one-step reaction, the reaction process is simple, an expensive and complex catalyst is not needed in the reaction, the reaction conditions are mild, simple and environment-friendly, and the green chemical concept is met.
Preferably, said R is1The structure of the substituted 3-indoleacetic acid compound is shown as a formula II:
wherein R is1Is hydrogen, halogen, alkyl or alkoxy.
Preferably, said R is2The substituted sodium sulfinate compound has a structure shown in a formula III:
R2-SO2Na
III；
wherein R is2Is alkyl, phenyl or substituted phenyl; the substituent in the substituted phenyl is halogen or alkyl.
More preferably, said R1Is one or more of hydrogen, halogen, methyl or methoxy; r2Is alkyl, phenyl or substituted phenyl; the substituent in the substituted phenyl is halogen, methyl, ethyl or tertiary butyl.
More preferably, said R1Is hydrogen, methyl or methoxy; r2Is alkyl, phenyl or substituted phenyl; the substituent in the substituted phenyl is methyl or ethyl.
Preferably, the copper catalyst is one of copper acetate, copper oxide, copper trifluoroacetate, copper trifluoromethanesulfonate, copper bromide or cuprous iodide.
Preferably, the copper catalyst is one of copper acetate and cuprous iodide; more preferably, the catalyst is copper acetate.
Preferably, the temperature of the heating reaction is 100-115 ℃; more preferably, the temperature of the heating reaction is 115 ℃.
Preferably, said R is1Substituted 3-indoleacetic acid compounds and R2The molar ratio of the substituted sodium sulfinate compound is 1: 1-2; more preferably, the molar ratio is 1: 2.
Preferably, said R is1The molar ratio of the substituted 3-indoleacetic acid compound to the catalyst is 1: 1-2; more preferably, the molar ratio is 1: 2.
Preferably, after the reaction is finished, extracting the reaction solution by using ethyl acetate, collecting an organic phase, and concentrating to obtain a crude product; and then carrying out column chromatography separation on the crude product to obtain the 3-sulfone methyl-1H-indole compound shown in the formula I.
Preferably, the mobile phase of the column chromatography is petroleum ether and ethyl acetate, and gradient elution is carried out according to the volume ratio of (2-10): 1; more preferably, the mobile phase is a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 2: 1.
Compared with the prior art, the invention has the following beneficial effects:
the method takes a substituted 3-indoleacetic acid compound and a substituted sodium sulfinate compound as raw materials, adopts a copper catalyst, takes N, N-dimethylformamide or dimethyl sulfoxide as a solvent for reaction, and obtains a 3-sulfone methyl-1H-indole compound through one-step reaction under the protection of nitrogen; according to the method, N-dimethylformamide or dimethyl sulfoxide is used as a solvent, so that the use of a large amount of organic solvents is avoided, and a copper catalyst is adopted, so that the use of an expensive and complex catalyst is avoided; the reaction condition is mild, the reaction process is simple, and the green chemical concept is met.
The post-treatment of the reaction is simple, and the high-purity 3-sulfone methyl-1H-indole compound can be obtained only by simple extraction, concentration and column chromatography; has very wide application prospect for the preparation and the application of the 3-sulfone methyl-1H-indole compound.
Detailed Description
The present invention is further described in detail below with reference to specific examples, which are provided for illustration only and are not intended to limit the scope of the present invention. The test methods used in the following examples are all conventional methods unless otherwise specified; the materials, reagents and the like used are, unless otherwise specified, commercially available reagents and materials.
Example 1
The influence of the types of the catalyst, the solvent and the additive on the reaction is researched, and the specific process is as follows:
3-indoleacetic acid and sodium p-toluenesulfinate are used as reaction raw materials, a catalyst, a solvent and an additive are shown in table 1, the reaction is carried out for 6 hours in a 25mL reaction tube, then the reaction tube is cooled to room temperature, a proper amount of water is added, an organic phase is collected by three times of extraction with ethyl acetate, the solvent is removed by decompression and rotary evaporation of a rotary evaporator, and then the product is obtained by separation and purification of a thin-layer plate, wherein the thin-layer plate developing agent is a mixed solvent of petroleum ether and ethyl acetate with the volume ratio of (2-10) to 1.
TABLE 1 Effect of different catalysts, solvents and additives on the reaction
Note: the "trace" in the table indicates trace, i.e. not detectable.aThe reaction temperature was 100 ℃.
From the above reactions under different conditions, the above reactions can occur when the catalyst is one of cupric acetate and cuprous iodide, but when the catalyst is different, the yield of the product is affected, and when the catalyst is cuprous iodide, the yield of the product is only 60%, wherein when the catalyst is cupric acetate, the yield of the product is the highest, up to 90%.
When the solvent is a commonly used organic solvent such as dioxane, tolumene or DCE, the reaction does not occur or occurs in a smaller amount, and the yield of the product is extremely low; but when the reaction solvent is DMF or DMSO, the yield of the reaction product is higher; indicating that the above reaction is likely to occur in DMF or DMSO.
When the reaction temperature is 100 ℃ to 115 ℃, the reaction can all occur, but when the reaction temperature is different, the yield of the product is different, and when the reaction temperature is 115 ℃, the yield of the reaction product is the highest.
From the above reaction, it can be seen that the optimum reaction conditions are obtained when the catalyst is copper acetate, the reaction solvent is N, N-dimethylformamide, the reaction temperature is 115 ℃ and the nitrogen gas is used for protection.
Example 2
The reaction was carried out under the above-mentioned optimum reaction conditions, and different reaction materials were replaced, and specific reaction materials are shown in Table 2, wherein the dosage of the substituted 3-indoleacetic acid is 0.5mmol, the dosage of the substituted sodium sulfinate is 1mmol, the dosage of the copper acetate is 1mmol, the dosage of the N, N-dimethylformamide is 3mL, reacting in a 25mL reaction tube at 115 ℃ under the protection of nitrogen for 6h, then stopping heating and stirring, cooling to room temperature, adding a proper amount of water, extracting for three times by using ethyl acetate, collecting an organic phase, and performing reduced pressure rotary evaporation to remove the solvent, and then separating and purifying through a thin-layer plate to obtain a product, wherein the volume ratio of the used thin-layer plate developing agent is (2-10): 1 petroleum ether: and (3) preparing the 3-p-toluenesulfonylmethyl-1H-indole compound with different substituents by using a mixed solvent of ethyl acetate.
TABLE 2 preparation of 3-p-toluenesulfonylmethyl-1H-indole compounds with different substituents
The characterization data for the compounds of examples 2 to 16 are as follows:
example 2:1H NMR(400MHz,CDCl3)8.39(s,1H),7.56(d,J＝7.9Hz,2H),7.30(dd,J＝14.9,8.1Hz,2H),7.16(dd,J＝13.0,7.8Hz,3H),7.03(d,J＝8.1Hz,2H),4.51(s,2H),2.37(s,3H).13C NMR(100MHz,CDCl3)144.4,135.7,135.4,129.4,128.5,126.9,125.9,122.4,120.1,118.5,111.3,102.8,54.5,21.5.
example 3:1H NMR(400MHz,CDCl3)8.19(s,1H),7.51(d,J＝8.2Hz,2H),7.22–7.17(m,2H),7.15(d,J＝8.3Hz,2H),7.06(t,J＝7.2Hz,1H),6.96(t,J＝7.5Hz,1H),4.44(s,2H),2.37(s,3H),2.07(s,3H).13C NMR(100MHz,CDCl3)144.4,135.9,135.4,134.8,129.4,128.6,128.1,121.4,119.9,117.9,110.3,99.1,54.9,21.5,11.4.
example 4:1H NMR(400MHz,CDCl3)8.66(s,1H),7.61(d,J＝8.2Hz,2H),7.31(s,1H),7.21(t,J＝7.9Hz,3H),7.03–6.96(m,2H),4.91(s,2H),2.38(s,3H).13C NMR(100MHz,CDCl3)144.5,137.2,135.8,129.5,128.5,127.7,125.7,123.5,122.8,121.3,110.4,102.1,54.0,21.6.
example 5:1H NMR(400MHz,Chloroform-d)8.52(s,1H),7.56(d,J＝8.2Hz,2H),7.17(dd,J＝8.1,4.1Hz,3H),6.96–6.91(m,3H),4.48(s,2H),2.37(s,3H),2.32(s,3H).13C NMR(100MHz,CDCl3)144.4,135.3,134.1,129.4,129.1,128.6,127.1,126.2,123.8,117.9,111.0,101.8,54.6,21.4,21.3.
example 6:1H NMR(400MHz CDCl3,)8.35(s,1H),7.55(d,J＝8.0Hz,2H),7.18(t,J＝8.1Hz,3H),6.99(s,1H),6.79(d,J＝10.7Hz,1H),6.62(s,1H),4.48(s,2H),3.71(s,3H),2.37(s,3H).13C NMR(100MHz,CDCl3)154.4,144.5,135.4,130.8,129.4,128.6,127.4,126.6,112.9,112.1,102.6,99.9,55.5,54.7,21.5.
example 7:1H NMR(400MHz,CDCl3)8.19(s,1H),7.56(d,J＝8.0Hz,2H),7.16(dd,J＝15.0,8.3Hz,3H),6.92(s,1H),6.79(s,1H),6.69(d,J＝8.6Hz,1H),4.47(s,2H),3.80(s,3H),2.38(s,3H).13C NMR(100MHz,CDCl3)156.7,144.4,136.6,135.4,129.4,128.5,124.6,121.3,119.4,110.3,102.9,94.5,55.6,54.6,21.6.
example 8:1H NMR(400MHz,CDCl3)8.02(s,1H),7.51(d,J＝8.1Hz,2H),7.15(d,J＝8.0Hz,2H),7.08(d,J＝8.7Hz,1H),6.71(d,J＝8.7Hz,1H),6.52(d,J＝2.0Hz,1H),4.42(s,2H),3.70(s,3H),2.37(s,3H),2.09(s,3H).13C NMR(100MHz,CDCl3)154.3,144.4,136.6,135.5,129.7,129.4,128.7,128.6,111.5,111.0,99.7,99.2,55.5,54.1,21.5,11.5.
example 9:1H NMR(400MHz,CDCl3)8.37(s,1H),7.68(d,J＝7.4Hz,2H),7.54(t,J＝7.4Hz,1H),7.38(t,J＝7.8Hz,2H),7.32(d,J＝8.2Hz,1H),7.24(s,1H),7.15(t,J＝7.5Hz,1H),7.02(dd,J＝17.0,9.3Hz,2H),4.54(s,2H).13C NMR(100MHz,CDCl3)138.2,135.7,133.5,128.8,128.5,126.9,125.9,122.5,120.3,118.5,111.3,102.7,54.4.
example 10:1H NMR(400MHz,CDCl3)8.39(s,1H),7.64(dd,J＝8.6,5.2Hz,2H),7.33(d,J＝8.2Hz,1H),7.24(d,J＝8.0Hz,1H),7.16(t,J＝7.5Hz,1H),7.07–7.00(m,4H),4.53(s,2H).13C NMR(100MHz,CDCl3)165.8(d,J＝254Hz),135.7,134.1,131.4(d,J＝9Hz),126.7,125.9,122.6,120.4,118.3,116.1(d,J＝22Hz),111.3,54.6.
example 11:1H NMR(400MHz,CDCl3)8.51(s,1H),7.59(d,J＝7.6Hz,2H),7.38–7.25(m,4H),7.09(d,J＝6.5Hz,2H),6.93(s,1H),4.51(s,2H),1.29(s,9H).13C NMR(100MHz,CDCl3)157.5,135.7,135.2,128.4,126.9,126.1,125.8,122.2,120.1,118.2,111.3,102.6,54.6,35.1,31.0.
example 12:1H NMR(400MHz,CDCl3)8.36(s,1H),7.57(d,J＝8.0Hz,2H),7.31(d,J＝8.1Hz,1H),7.16(dd,J＝16.1,8.0Hz,4H),7.07(s,1H),6.98(t,J＝7.4Hz,1H),4.51(s,2H),2.66(q,J＝7.6Hz,2H),1.21(t,J＝7.6Hz,3H).13C NMR(100MHz,CDCl3)150.6,135.7,135.5,128.7,128.3,127.0,125.9,122.4,120.2,118.5,111.3,102.9,54.5,28.8,15.2.
example 13:1H NMR(400MHz,CDCl3)8.46(s,1H),7.51(d,J＝7.4Hz,1H),7.46(s,1H),7.35–7.27(m,3H),7.23(d,J＝8.0Hz,1H),7.14(t,J＝7.5Hz,1H),7.05(s,1H),7.00(t,J＝7.5Hz,1H),4.52(s,2H),2.25(s,3H).13C NMR(100MHz,CDCl3)139.1,138.1,135.7,134.2,128.9,128.7,126.9,126.0,125.5,122.3,120.1,118.4,111.3,102.5,54.5,21.0.
example 14:1H NMR(400MHz,CDCl3)8.46(s,1H),7.65(d,J＝7.7Hz,1H),7.42(d,J＝8.0Hz,1H),7.37(s,1H),7.26–7.18(m,2H),4.46(s,2H),2.74(s,3H).13C NMR(100MHz,CDCl3)136.0,126.6,125.9,122.8,120.7,118.2,111.7,102.7,52.6,38.8.
example 15:1H NMR(400MHz,CDCl3)8.61(s,1H),7.64(d,J＝7.7Hz,1H),7.39(d,J＝7.9Hz,1H),7.30(s,1H),7.24–7.17(m,2H),4.43(s,2H),2.87(q,J＝7.5Hz,2H),1.34(t,J＝7.5Hz,3H).13C NMR(100MHz,CDCl3)136.0,126.7,125.9,122.7,120.6,118.2,111.7,102.3,50.2,45.0,6.3.
example 16:1H NMR(400MHz,CDCl3)8.43(s,1H),7.68(d,J＝7.7Hz,1H),7.44–7.35(m,2H),7.21(dt,J＝14.6,7.4Hz,2H),4.48(s,2H),2.21(s,1H),1.18(d,J＝4.2Hz,2H),0.89(d,J＝7.1Hz,2H).13C NMR(100MHz,CDCl3)135.9,127.1,125.9,122.7,120.5,118.4,111.6,102.8,51.4,28.1,4.9.
according to the method, 3-sulfone methyl-1H-indole compounds with various substituents can be prepared, and the preparation process is simple, mild in condition and environment-friendly.
It should be finally noted that the above examples are only intended to illustrate the technical solutions of the present invention, and not to limit the scope of the present invention, and that other variations and modifications based on the above description and thought may be made by those skilled in the art, and that all embodiments need not be exhaustive. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (10)
1. A green synthesis method of a 3-sulfone methyl-1H-indole compound is characterized in that the structure of the 3-sulfone methyl-1H-indole compound is shown as a formula I:
wherein R is1Is hydrogen, halogen, alkyl or alkoxy; r2Is alkyl, phenyl or substituted phenyl;
the preparation process comprises the following steps: with R1Substituted 3-indoleacetic acid compounds and R2The substituted sodium sulfinate compound is used as a raw material, a copper catalyst is adopted, N-dimethylformamide or dimethyl sulfoxide is used as a solvent, nitrogen is used for protection, and the reaction is heated to generate the 3-sulfone methyl-1H-indole compound shown in the formula I.
2. The green synthesis method of 3-sulfonemethyl-1H-indole compound according to claim 1, wherein R is1The structure of the substituted 3-indoleacetic acid compound is shown as a formula II:
wherein R is1Is hydrogen, halogen, alkyl or alkoxy.
3. The green synthesis method of 3-sulfonemethyl-1H-indole compound according to claim 1, wherein R is2The structure of the substituted sodium sulfinate compound is shown as the formula III:
wherein R is2Is alkyl, phenyl or substituted phenyl.
4. A green synthesis method of 3-sulfonemethyl-1H-indole compound according to any one of claims 1 to 3, wherein R is1Is one or more of hydrogen, halogen, methyl or methoxy; r2Is alkyl, phenyl or substituted phenyl; the substituent in the substituted phenyl is halogen, methyl, ethyl or tertiary butyl.
5. The green synthesis method of the 3-sulfonemethyl-1H-indole compound according to claim 1, wherein the copper catalyst is one of copper acetate, copper oxide, copper trifluoroacetate, copper trifluoromethanesulfonate, copper bromide or copper iodide.
6. The green synthesis method of the 3-sulfonemethyl-1H-indole compound of claim 5, wherein the catalyst is copper acetate.
7. The green synthesis method of the 3-sulfonemethyl-1H-indole compound according to claim 1, wherein the temperature of the heating reaction is between 100 ℃ and 115 ℃.
8. The green synthesis method of 3-sulfonemethyl-1H-indole compound according to claim 1, wherein R is1Substituted 3-indoleacetic acid compounds and R2The molar ratio of the substituted sodium sulfinate compound is 1: 1-2; the R is1The molar ratio of the substituted 3-indoleacetic acid compound to the catalyst is 1: 1-2.
9. The green synthesis method of the 3-sulfonemethyl-1H-indole compound as claimed in any one of claims 1 to 8, wherein after the reaction is finished, the reaction solution is extracted with ethyl acetate, the organic phase is collected and concentrated to obtain a crude product; and then carrying out column chromatography separation on the crude product to obtain the 3-p-sulfone methyl-1H-indole compound shown in the formula I.
10. The green synthesis method of the 3-sulfone methyl-1H-indole compound as claimed in claim 9, wherein the mobile phase of column chromatography is petroleum ether and ethyl acetate, and gradient elution is performed at a volume ratio of (2-10): 1.
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